Lakeville Vacation Rentals from ￥24,035: Search Short-Term Rentals

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Our top choices for Lakeville vacation rentals

1. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

￥65,180 total

includes taxes & fees

Sep 28 - Sep 29

2. A Country Lodge Straight Out of the Pages of a Great Novel

Pine Plains

Hessie S.

￥206,904 total

includes taxes & fees

Oct 17 - Oct 18

3. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Kent

Lisa F.

￥38,756 total

includes taxes & fees

Sep 21 - Sep 22

4. Riverside Retreat in the Berkshires

Great Barrington

Kelly B.

￥46,565 total

includes taxes & fees

Sep 29 - Sep 30

5. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Stanfordville

￥105,222 total

includes taxes & fees

Sep 17 - Sep 18

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Great Barrington

Kristin O.

￥42,903 total

includes taxes & fees

Sep 17 - Sep 18

7. Pristine Cozy Walkable Downtown 2BR Getaway

Torrington

Amanda T.

￥43,721 total

includes taxes & fees

Sep 29 - Sep 30

8. Home in Great Barrington

Great Barrington

HEATHER G.

￥45,280 total

includes taxes & fees

Sep 17 - Sep 18

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Top Lakeville Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good

"Basically furnished . Great staff. Easy checkin and check out. Good breakfast. Lots of options. Comfortable queen beds. Convenient to restaurants, stores etc."

The Little Lion

8/10 Good

"Nice, old-school motel, where you park out front. There appear to be about 17 units and on the night we were there, more than half were occupied— and all seemed to have a dog! Very pet-friendly, with plenty of room to walk your pooch! The beds and bedding were very comfortable and the room had a mini fridge and microwave. While simply furnished, everything was spotless. I would have given a higher score, but was a little put off when we arrived about 45 minutes before check in and were told we would have to wait until 3pm for them to unlock our door. There is no staff onsite, so I called. While I know hotels have check in times for a reason, if the room is ready and the guest is outside the door, a little flexibility is always a good business practice! But the location is great. The motel is set well back from the road, so there was no traffic noise. A parking area for Monument Mountain is just a few hundred yards away for hikers. We loved the Little Lion and will definitely return."

Summer Lake Cottage, private beach, Berkshire Hills, small village

10/10 Excellent

"We had such a great stay here for my 25th birthday weekend. The cabin was exactly what we were looking for and was a great place to spend the weekend with a group of friends. It was comfortable, clean, and had everything we needed for a relaxing getaway.The space was especially great for having a larger group together, with plenty of room to hang out, cook, eat, and enjoy the property. The cabin had a really cozy atmosphere and made the weekend feel like an actual getaway rather than just staying somewhere overnight.Our host was also great and made everything easy from check-in through check-out. We’d definitely stay here again and would recommend it to anyone looking for a fun cabin getaway with friends or family!"

Find out more about Lakeville

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Frequently asked questions

Can I find vacation rentals in Lakeville?

Yes, we offer vacation rentals close to well known attractions in Lakeville, or you can select a secluded option if you'd like a relaxing place to stay. Lakeville is known for its restaurants and museums.

What are some of the best vacation home rentals that Lakeville has to offer?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This vacation home near Lakeville offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Lakeville?

Expedia has 15 vacation rentals for your stay in Lakeville.

What’s there to see and do in Lakeville?

While exploring the area, visit family-friendly sights like Harney and Sons Tea Tasting Room, or get outside and enjoy nature at Gay Woods Hill. Holley-Williams House Museum and Lime Rock Park are other places to visit while you're in town.

What’s a vacation rental in Lakeville like?

A vacation rental is a private property you can book for a few weeks or just a few days in Lakeville. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips.

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Check prices for these dates

Our top choices for Lakeville vacation rentals

1. Cheerful 3-bedroom cottage with woodstove

2. A Country Lodge Straight Out of the Pages of a Great Novel

3. Mid Century Modern Studio w/ Full Kitchen - Newly Built

4. Riverside Retreat in the Berkshires

5. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

7. Pristine Cozy Walkable Downtown 2BR Getaway

8. Home in Great Barrington

9. Ideal location for summer and winter activities with plenty of outdoor space.

10. Fantastic 2-bedroom house with AC in quaint Hillsdale.

11. Cozy. Clean. Free bagel shop. 3 Fireplaces.

12. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

13. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

14. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

15. Art House 3 Beds Close to Warner Theater

16. Cozy 1-bedroom studio in serene Great Barrington with AC

17. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

18. Gorgeous Mountain Views Retreat: Family & Nature

19. The George is an elegant restored home in the Hudson Valley

Find vacation rentals that suit your style

Top Lakeville Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Little Cat Lodge

The Little Lion

the Alander

Locust Tree Bed and Breakfast LLC

Quality Inn Great Barrington

Monument Mountain Motel

Summer Lake Cottage, private beach, Berkshire Hills, small village

The Litchfield Inn

Find out more about Lakeville

Frequently asked questions

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